(S)-1-(4-chlorophenyl)-(1H-imidazol-1-yl)ethyl 4-(4-nitrophenylthio)phenylcarbamate

ID: ALA3318324

PubChem CID: 118708815

Max Phase: Preclinical

Molecular Formula: C24H19ClN4O4S

Molecular Weight: 494.96

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(Sc2ccc([N+](=O)[O-])cc2)cc1)O[C@H](Cn1ccnc1)c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C24H19ClN4O4S/c25-18-3-1-17(2-4-18)23(15-28-14-13-26-16-28)33-24(30)27-19-5-9-21(10-6-19)34-22-11-7-20(8-12-22)29(31)32/h1-14,16,23H,15H2,(H,27,30)/t23-/m1/s1

Standard InChI Key:  RMVSYBKSIWTOER-HSZRJFAPSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
   15.8288   -9.8721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6030  -10.5798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0116   -9.8721    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0116  -11.2875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7858  -10.5798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3772   -9.8721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7858   -9.1644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7096   -7.7101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1023   -7.1633    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3946   -7.5719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5645   -8.3712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3772   -8.4566    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5600   -9.8721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1514  -10.5798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3342  -10.5798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9256   -9.8721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3342   -9.1644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1514   -9.1644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1084   -9.8721    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.2329  -10.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0493  -10.5795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4587   -9.8713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0457   -9.1612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2306   -9.1643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2759   -9.8702    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.6835   -9.1619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4982   -9.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9058   -8.4558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4962   -7.7476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6748   -7.7513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2709   -8.4593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9039   -7.0364    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4934   -6.3298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7211   -7.0342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  2  4  2  0
  2  5  1  0
  1  3  1  0
  6  7  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  8 12  1  0
  7 12  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 13 18  2  0
 16 19  1  0
  6 13  1  0
  6  5  1  1
  1 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24  1  1  0
 22 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
 32 33  2  0
 32 34  1  0
 29 32  1  0
M  CHG  2  32   1  34  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3318324

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 494.96

Molecular Weight (Monoisotopic): 494.0816

AlogP: 6.59

#Rotatable Bonds: 8

Polar Surface Area: 99.29

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.97

CX Basic pKa: 6.77

CX LogP: 6.25

CX LogD: 6.19

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.22

Np Likeness Score: -1.45

References

1. Friggeri L, Hargrove TY, Rachakonda G, Williams AD, Wawrzak Z, Di Santo R, De Vita D, Waterman MR, Tortorella S, Villalta F, Lepesheva GI..  (2014)  Structural basis for rational design of inhibitors targeting Trypanosoma cruzi sterol 14α-demethylase: two regions of the enzyme molecule potentiate its inhibition.,  57  (15): [PMID:25033013] [10.1021/jm500739f]

2. De Vita D, Pandolfi F, Cirilli R, Scipione L, Di Santo R, Friggeri L, Mori M, Fiorucci D, Maccari G, Arul Christopher RS, Zamperini C, Pau V, De Logu A, Tortorella S, Botta M..  (2016)  Discovery of in vitro antitubercular agents through in silico ligand-based approaches.,  121  [PMID:27240272] [10.1016/j.ejmech.2016.05.032]

Source

Source(1):

• Scientific Literature